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Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions

Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in D...

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Detalles Bibliográficos
Autores principales: Chen, Xin, Bian, Yunyun, Mo, Baichuan, Sun, Peng, Chen, Chunxia, Peng, Jinsong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055228/
https://www.ncbi.nlm.nih.gov/pubmed/35517475
http://dx.doi.org/10.1039/d0ra04592f
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author Chen, Xin
Bian, Yunyun
Mo, Baichuan
Sun, Peng
Chen, Chunxia
Peng, Jinsong
author_facet Chen, Xin
Bian, Yunyun
Mo, Baichuan
Sun, Peng
Chen, Chunxia
Peng, Jinsong
author_sort Chen, Xin
collection PubMed
description Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)(2)/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO(4) and KHCO(3). Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives.
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spelling pubmed-90552282022-05-04 Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions Chen, Xin Bian, Yunyun Mo, Baichuan Sun, Peng Chen, Chunxia Peng, Jinsong RSC Adv Chemistry Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)(2)/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO(4) and KHCO(3). Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. The Royal Society of Chemistry 2020-06-30 /pmc/articles/PMC9055228/ /pubmed/35517475 http://dx.doi.org/10.1039/d0ra04592f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chen, Xin
Bian, Yunyun
Mo, Baichuan
Sun, Peng
Chen, Chunxia
Peng, Jinsong
Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title_full Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title_fullStr Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title_full_unstemmed Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title_short Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
title_sort copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential chan–lam and cross-dehydrogenative coupling reactions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055228/
https://www.ncbi.nlm.nih.gov/pubmed/35517475
http://dx.doi.org/10.1039/d0ra04592f
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